Near infrared zinc ion fluorescent probe compound, and preparation method and applications thereof

A fluorescent probe and zinc ion technology, which is applied in the field of fluorescent probes for metal ion detection, can solve the problems of long reaction time, poor selectivity of zinc ion fluorescent probes, poor water solubility, etc., and achieve short response time and strong anti-interference ability , easy to store effects

Active Publication Date: 2019-06-18
JIANGSU UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Nevertheless, many reported fluorescent probes for zinc ions still hav...

Method used

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  • Near infrared zinc ion fluorescent probe compound, and preparation method and applications thereof
  • Near infrared zinc ion fluorescent probe compound, and preparation method and applications thereof
  • Near infrared zinc ion fluorescent probe compound, and preparation method and applications thereof

Examples

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Embodiment 1

[0052] (1) Preparation of (E)-2-(3-(3-formyl-4-hydroxy)vinyl)-5,5-dimethylcyclohex-2-en-1-yl)malononitrile (formula ⅡIntermediate)

[0053] To a 100mL round bottom flask was added malononitrile (1.87g, 28.3mmol), isophorone (3.9g, 28.3mmol), N,N-dimethylformamide (10mL), piperidine (380μL, 3.84mmol), acetic acid (28μL, 0.19mmol), acetic anhydride (18μL, 0.5mmol), stir at room temperature for 1~2h, continue stirring at 80~85℃ for 1~2h, and then add p-hydroxybenzaldehyde ( 3.45g, 28.7mmol), stirred at 80~85℃ for 1~2h, while hot, pour the reactant into 200~220mL water containing 6~8mL concentrated hydrochloric acid, stir, filter with suction, and wash the solid with deionized water 6~ 8 times, the obtained solid was recrystallized with acetonitrile to obtain (E)-2-(3-(4-hydroxystyryl)-5,5-dimethylcyclohex-2-en-1-ylidene)propane Dinitrile (Intermediate of Formula IV).

[0054] Add (E)-2-(3-(4-hydroxystyryl)-5,5-dimethylcyclohex-2-en-1-ylidene)malononitrile (1.16g) to a 100mL round b...

Embodiment 2

[0062] The near-infrared zinc ion fluorescent probe compound described in Example 1 was used for testing.

[0063] Dissolve the near-infrared zinc ion fluorescent probe compound in DMSO-H 2 In O(v / v=3:2) solution, the concentration is 10μM, and the concentration of other metal ions is 50μM. Test with fluorescence spectrometer and ultraviolet spectrophotometer. The maximum excitation wavelength of the fluorescent probe is 502nm and the maximum emission wavelength is 670nm. .

[0064] Such as figure 1 , Adding zinc ions (Zn 2+ ) UV absorption and fluorescence spectra before and after, the probe compound itself has an UV absorption peak at 434nm, but after the probe compound molecule is complexed with zinc ions, a new UV absorption peak appears at 502nm, and the probe compound itself is at 670nm There is almost no fluorescence, but after the probe compound molecule is complexed with zinc ions, it produces strong fluorescence at 670nm, in the near-infrared region, and the Stokes shift...

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Abstract

The invention discloses a near infrared zinc ion fluorescent probe compound, and a preparation method thereof. The preparation method comprises following steps: malononitrile and isophorone are dissolved in an organic solvent for reaction with piperidine, acetic acid, acetic anhydride, and p-hydroxy benzaldehyde, and an obtained product is dissolved in trifluoroacetic acid for reaction with urotropine so as to obtain an intermediate represented by formula II; 5-amino-4, 6-dichloropyrimidine and 1-naphthylamine are added into an organic solvent, concentrated hydrochloric acid is added, reflux reaction is carried out, an obtained reaction product, acetic acid, polyphosphoric acid, and dodecyl trimethyl ammonium chloride are dissolved in phosphorous oxychloride, an obtained reaction substanceis dissolved in an organic solvent for reaction with hydrazine hydrate so as to obtain an intermediate represented by formula II; the intermediate represented by formula II and the intermediate represented by formula III are added into an organic solvent for reaction so as to obtain the near infrared zinc ion fluorescent probe compound (formula I). The near infrared zinc ion fluorescent probe compound is high in sensitivity, excellent in anti-interference performance, and can be widely used for zinc ion detection.

Description

Technical field [0001] The invention belongs to the technical field of fluorescent probes for metal ion detection, and specifically relates to a near-infrared zinc ion fluorescent probe compound and a preparation method and application thereof. Background technique [0002] As the second most abundant metal element in the human body, zinc (Zn) plays a vital role in many biological processes, including gene expression, cell growth, cell division, cell metabolism, DNA replication and repair. Excess or deficiency of zinc ions can cause many diseases, such as Alzheimer's disease, which is increasing the incidence of many types of cancer, such as epilepsy, ischemic stroke and infant diarrhea. Therefore, in order to maintain human health, it is very important to develop methods to effectively identify zinc ions in drinking water and living cells. [0003] Currently commonly used zinc ion detection methods include atomic absorption spectroscopy (AAS), atomic emission spectroscopy (AES) i...

Claims

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Application Information

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IPC IPC(8): C07D473/34C09K11/06G01N21/64
Inventor 伍国伟陆鸿飞金鑫鑫陈葳张维霞朱凌青王正义
Owner JIANGSU UNIV OF SCI & TECH
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